US5958352A - Abatement of hydrogen sulfide with an aldehyde ammonia trimer - Google Patents

Abatement of hydrogen sulfide with an aldehyde ammonia trimer Download PDF

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Publication number
US5958352A
US5958352A US08/792,961 US79296197A US5958352A US 5958352 A US5958352 A US 5958352A US 79296197 A US79296197 A US 79296197A US 5958352 A US5958352 A US 5958352A
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substrate
ppm
aldehyde ammonia
trimers
hydrogen sulfide
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US08/792,961
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English (en)
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Michael Callaway
Gordon T. Rivers
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Baker Hughes Holdings LLC
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Baker Hughes Inc
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Assigned to BAKER HUGHES INCORPORATED reassignment BAKER HUGHES INCORPORATED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CALLAWAY, MICHAEL, RIVERS, GORDON
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
    • C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
    • C10L3/10—Working-up natural gas or synthetic natural gas
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
    • C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
    • C10G21/12—Organic compounds only
    • C10G21/20—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
    • C10G29/20—Organic compounds not containing metal atoms

Definitions

  • the invention relates to chemical compositions and methods for scavenging sulfhydryl compounds, particularly hydrogen sulfide (H 2 S), from "sour" aqueous and hydrocarbon substrates. More particularly, the invention relates to the use of aldehyde ammonia trimers as scavengers for sulfhydryl compounds in natural gas.
  • H 2 S hydrogen sulfide
  • H 2 S The removal of H 2 S from a liquid or gaseous hydrocarbon stream is a problem that has challenged many workers in many industries.
  • One such industry is the petroleum industry, where the H 2 S content of certain crudes from reservoirs in many areas of the world is too high for commercial acceptance.
  • the same is true of many natural gas streams.
  • H 2 S Hydrogen sulfide is highly flammable, toxic when inhaled, and strongly irritates the eyes and other mucous membranes.
  • sulfur-containing salts can deposit in and plug or corrode transmission pipes, valves, regulators, and the like. Flaring of natural gas that contains H 2 S does not solve the problem for gas streams because, unless the H 2 S is removed prior to flaring, the combustion products will contain unacceptable amounts of pollutants, such as sulfur dioxide (SO 2 )--a component of "acid rain.”
  • Hydrogen sulfide has an offensive odor, and natural gas containing H 2 S often is called “sour” gas.
  • the sweetening or scavenging of H 2 S from petroleum or natural gas is only one example of where H 2 S level reduction or removal must be performed. Many aqueous substrates also must be treated to reduce or remove H 2 S.
  • the present invention provides a method for scavenging H 2 S from aqueous and hydrocarbon substrates, preferably natural gas, using aldehyde ammonia trimers.
  • the scavenging agents of the present invention may be used to treat aqueous and hydrocarbon substrates that are rendered “sour” by the presence of "sulfhydryl compounds,” such as hydrogen sulfide (H 2 S), organosulfur compounds having a sulfhydryl (--SH) group, known as mercaptans, also known as thiols (R--SH, where R is a hydrocarbon group), thiol carboxylic acids (RCO--SH), dithio acids (RCS--SH), and related compounds.
  • sulfhydryl compounds such as hydrogen sulfide (H 2 S), organosulfur compounds having a sulfhydryl (--SH) group, known as mercaptans, also known as thiols (R--SH, where R is a hydrocarbon group), thiol carboxylic acids (RCO--SH), dithio acids (RCS--SH), and related compounds.
  • aqueous substrate refers to any “sour” aqueous substrate, including waste water streams in transit to or from municipal waste water treatment facilities, tanning facilities, and the like.
  • hydrocarbon substrate is meant to include unrefined and refined hydrocarbon products, including natural gas, derived from petroleum or from the liquefaction of coal, both of which contain hydrogen sulfide or other sulfur-containing compounds.
  • hydrocarbon substrate includes wellhead condensate as well as crude oil which may be contained in storage facilities at the producing field.
  • Hydrocarbon substrate also includes the same materials transported from those facilities by barges, pipelines, tankers, or trucks to refinery storage tanks, or, alternately, transported directly from the producing facilities through pipelines to the refinery storage tanks.
  • hydrocarbon substrate also includes refined products, interim and final, produced in a refinery, including distillates such as gasolines, distillate fuels, oils, and residual fuels.
  • distillates such as gasolines, distillate fuels, oils, and residual fuels.
  • hydrocarbon substrate also refers to vapors produced by the foregoing materials.
  • a wide variety of aqueous and hydrocarbon substrates can be treated using the scavenging agents of the present invention, a preferred substrate being natural gas.
  • the trimers preferably should be added to the substrate at a high enough temperature that the substrate is flowable for ease in mixing.
  • the treatment may take place at temperatures up to the temperature at which the material being treated begins to decompose. Preferred treatment temperatures are between ambient to about 65.6° C. (150° F.).
  • the scavenging agents of the present invention are aldehyde ammonia trimers that generally have the following formula: ##STR1## wherein R 1 , R 2 , and R 3 are independently selected from the group consisting of hydrogen and hydrocarbon groups having between about 1-8 carbon atoms, selected from the group consisting of straight, branched, and cyclic alkyl groups, aryl, alkaryl, and aralkyl groups, and heterocyclic alkyls containing oxygen or tertiary nitrogen as a ring constituent wherein none of R 1 , R 2 , or R 3 is an alkoxyalkylene substitutent.
  • R 1 , R 2 , and R 3 are methyl groups.
  • the aldehyde ammonia trimers of the present invention exhibit a high uptake capacity for hydrogen sulfide, and the raw materials required to manufacture the trimers are low cost materials.
  • Aldehyde ammonia trimers are commercially available in small quantities from Aldrich Chemical Co., Milwaukee, Wis. Aldehyde ammonia trimers also may be manufactured by reacting acetaldehyde with aqueous ammonia in a 1:1 molar ratio. Water or another solvent, such as methanol, can be used in the reaction to prevent solid trimer from precipitating out of the solution. The amount of water used may vary depending upon how the product will be used. For example, if the substrate will be hydrophobic, e.g., a dry oil phase, the trimer may be formulated in isopropanol rather than water. In the field, the trimer preferably should be used in a solution having an active concentration of about 2-30%, preferably about 10-20%.
  • the substrate is natural gas and the trimer is added at a stoichiometric ratio of at least one molecule of trimer per three molecules of H 2 S.
  • the ratio preferably should be somewhat higher than 1:3 to assure abatement of H 2 S.
  • the amount of H 2 S in the natural gas may be measured by standard means. For ease in measurement, about: one gallon of the 10-20% active trimer solution may be added for every pound of H 2 S.
  • the aqueous or hydrocarbon substrates should be treated with the scavenging agent until reaction with hydrogen sulfide, or with other sulfhydryl compounds, has produced a product in which the sulfhydryls in the vapor (or liquid) phase have been removed to an acceptable or specification grade product.
  • a sufficient amount of scavenging agent should be added to reduce the sulfhydryls in the vapor phase to at least about 4 ppm or less.
  • the effectiveness of the scavenging agent is tested in an apparatus known as a "bubble tower.”
  • the "bubble tower” is a transparent acrylic column having a preferred internal diameter of 1.25 inches.
  • a solution of the scavenging agent is placed in the column to a given height, and gas having a known composition is bubbled through the solution.
  • the gas contains 2000 ppm H 2 S, 1% CO 2 , and a balance of methane; the H 2 S content of the gas exiting the solution is measured at given time intervals; and, measurements are made using stain tubes obtained from Sensidyne Gastech, located in Largo, Fla.
  • foaming is observed for foaming and for precipitate formation, both of which are undesirable.
  • Foaming may be desirable for some applications; however, foaming generally is undesirable when treating natural gas in a bubble tower.
  • the amount of foaming that results using a given candidate generally may be altered using defoaming compositions.
  • foaming is given as a measure of column height. Basically, the less the increase in column height, the less foam has been generated by the candidate.
  • the uptake test determines the activity of a particular candidate by measuring the weight gain of the candidate before and after exposure to pure H 2 S gas. Basically, 100 grams of a 5% solution of candidate in water is placed in a graduated cylinder with a dispersion stone and the total weight of the solution and the cylinder is measured using a balance. Thereafter, pure H 2 S gas is bubbled through the cylinder at 1 scfh. The weight of the solution is monitored until the weight remains substantially constant. The total weight gain is a measure of the activity of the candidate.
  • Aldehyde trimer for use in the following experiments was prepared as follows. A 500 ml three-necked reaction flask containing 169.4 g of 28% by weight aqueous ammonia and equipped with a magnetic stirrer, a reflux condenser, a pressure equalizing dropping funnel, and a thermometer was cooled in an ice bath. Chilled acetaldehyde (122.8 g) was added dropwise at such a rate as to keep the internal temperature below 30° C. (86° F.) to yield a white suspension. The suspension wets dissolved by adding 107.6 g of methanol and 40.0 g of water to yield a colorless solution containing 27.25% by weight reaction product. Proton and carbon NMR spectroscopy performed on the solution before and after the dissolution in methanol and water confirmed that the primary reaction product was an aldehyde ammonia trimer having the following structure: ##STR2##
  • the aldehyde ammonia trimer prepared in Example 1 was used to scavenge sulfur-containing compounds from natural gas.
  • the efficacy of the aldehyde ammonia trimer was tested using the bubble tower test, described under "Experimental Procedures.”
  • the H 2 S concentration in the outlet gas and the change in height due to foaming are reflected in Table I:
  • Aldehyde ammonia trimer prepared as set out in Example 1, was used to scavenge sulfur-containing compounds from natural gas.
  • the efficacy of the aldehyde ammonia trimer was tested using the bubble tower test, described under "Experimental Procedures.”
  • the bubble tower used in this example had an internal diameter of 1.125" rather than 1.25".
  • Aldehyde ammonia trimer was prepared as set out in Example 1, and used to scavenge sulfur-containing compounds from natural gas. 17.0 gm of the resulting trimer was diluted to a total of 100 gm of solution in distilled water. The efficacy of the aldehyde ammonia trimer was tested using a bubble tower with an internal diameter of 1.25".
  • Aldehyde ammonia trimer was prepared as set out in Example 1, and the procedures given in Example 5 were repeated.
  • the H 2 S concentration in the outlet gas and the change in height due to foaming are reflected in Table IV:
  • the uptake test was performed on a 6% active solution of aldehyde ammonia trimer prepared as in Example 1 and the Uptake Test was performed.
  • the total H 2 S uptake was 4.6 gm.
  • Acetaldehyde trimer obtained from Aldrich Chemical Co. was used to prepare a 4.23% active solution and the Uptake Test was performed.
  • the total H 2 S uptake was 3.5 gm.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Treating Waste Gases (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US08/792,961 1995-06-06 1997-01-24 Abatement of hydrogen sulfide with an aldehyde ammonia trimer Expired - Fee Related US5958352A (en)

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US08/792,961 US5958352A (en) 1995-06-06 1997-01-24 Abatement of hydrogen sulfide with an aldehyde ammonia trimer

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EP (1) EP0748861B1 (fr)
CA (1) CA2177408C (fr)
DK (1) DK0748861T3 (fr)
NO (1) NO312439B1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020157989A1 (en) * 2001-04-25 2002-10-31 Clearwater, Inc. Treatment of hydrocarbons Containing Sulfides
US20060075956A1 (en) * 1999-09-24 2006-04-13 Vec Industries, L.L.C. Boat and method for manufacturing using resin transfer molding
US7211665B2 (en) 2001-11-09 2007-05-01 Clearwater International, L.L.C. Sulfide scavenger
US20070284288A1 (en) * 2001-11-09 2007-12-13 Gatlin Larry W Sulfide scavenger
US20080056974A1 (en) * 2006-09-01 2008-03-06 Baker Hughes Incorporated Fast, high capacity hydrogen sulfide scavengers
US20090065445A1 (en) * 2007-09-12 2009-03-12 Guard Products Llc Aromatic imine compounds for use as sulfide scavengers
US20110155646A1 (en) * 2008-09-02 2011-06-30 Karas Lawrence John Process for removing hydrogen sulfide in crude oil
US8357306B2 (en) 2010-12-20 2013-01-22 Baker Hughes Incorporated Non-nitrogen sulfide sweeteners
US9278307B2 (en) 2012-05-29 2016-03-08 Baker Hughes Incorporated Synergistic H2 S scavengers
US9463989B2 (en) 2011-06-29 2016-10-11 Baker Hughes Incorporated Synergistic method for enhanced H2S/mercaptan scavenging
US20170153269A1 (en) * 2015-11-30 2017-06-01 International Business Machines Corporation Poly(thioaminal) probe based lithography
US9765188B2 (en) 2015-11-02 2017-09-19 International Business Machines Corporation High molecular weight polythioaminals from a single monomer
US9879118B2 (en) 2015-10-05 2018-01-30 International Business Machines Corporation Polymers from stabilized imines
US10080806B2 (en) 2015-08-19 2018-09-25 International Business Machines Corporation Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents

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Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20060075956A1 (en) * 1999-09-24 2006-04-13 Vec Industries, L.L.C. Boat and method for manufacturing using resin transfer molding
US20020157989A1 (en) * 2001-04-25 2002-10-31 Clearwater, Inc. Treatment of hydrocarbons Containing Sulfides
US7211665B2 (en) 2001-11-09 2007-05-01 Clearwater International, L.L.C. Sulfide scavenger
US20070284288A1 (en) * 2001-11-09 2007-12-13 Gatlin Larry W Sulfide scavenger
US8562820B2 (en) 2001-11-09 2013-10-22 Clearwater International, L.L.C. Sulfide scavenger
US20080056974A1 (en) * 2006-09-01 2008-03-06 Baker Hughes Incorporated Fast, high capacity hydrogen sulfide scavengers
US7438877B2 (en) 2006-09-01 2008-10-21 Baker Hughes Incorporated Fast, high capacity hydrogen sulfide scavengers
US20090065445A1 (en) * 2007-09-12 2009-03-12 Guard Products Llc Aromatic imine compounds for use as sulfide scavengers
WO2009035570A3 (fr) * 2007-09-12 2009-06-18 Custom Blenders Inc Composés d'imines aromatiques utilisables en tant que piégeurs de sulfure
US7985881B2 (en) 2007-09-12 2011-07-26 Guard Products Llc Aromatic imine compounds for use as sulfide scavengers
US8337792B2 (en) 2007-09-12 2012-12-25 Guard Products Llc Aromatic imine compounds for use as sulfide scavengers
WO2009035570A2 (fr) * 2007-09-12 2009-03-19 Custom Blenders, Inc. Composés d'imines aromatiques utilisables en tant que piégeurs de sulfure
US20110155646A1 (en) * 2008-09-02 2011-06-30 Karas Lawrence John Process for removing hydrogen sulfide in crude oil
US8357306B2 (en) 2010-12-20 2013-01-22 Baker Hughes Incorporated Non-nitrogen sulfide sweeteners
US9463989B2 (en) 2011-06-29 2016-10-11 Baker Hughes Incorporated Synergistic method for enhanced H2S/mercaptan scavenging
US9278307B2 (en) 2012-05-29 2016-03-08 Baker Hughes Incorporated Synergistic H2 S scavengers
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EP0748861A1 (fr) 1996-12-18
EP0748861B1 (fr) 2000-04-05
NO962323D0 (no) 1996-06-05
NO312439B1 (no) 2002-05-13
CA2177408C (fr) 2001-12-11
NO962323L (no) 1996-12-09
CA2177408A1 (fr) 1996-12-07
DK0748861T3 (da) 2000-08-21

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